Dichloromethane → 1-[3,3-Bis(3-chlorophenyl)acryloyl]-4-(3,4-dimethoxybenzoyl)piperazine

HRID 2380700Notes

Reaction equation

HRID 2380700 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[C:21]([C:25]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([Cl:41])[CH:36]=2)=[CH:26][C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[O:28])[CH:22]=[CH:23][CH:24]=1.C(Cl)Cl.[CH3:45][O:46][C:47]1[CH:48]=[C:49]([CH:53]=[CH:54][C:55]=1[O:56][CH3:57])[C:50](O)=[O:51]>C(N(CC)CC)C>[Cl:41][C:37]1[CH:36]=[C:35]([C:25]([C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[CH:20]=2)=[CH:26][C:27]([N:29]2[CH2:34][CH2:33][N:32]([C:50](=[O:51])[C:49]3[CH:53]=[CH:54][C:55]([O:56][CH3:57])=[C:47]([O:46][CH3:45])[CH:48]=3)[CH2:31][CH2:30]2)=[O:28])[CH:40]=[CH:39][CH:38]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7121Veratric AcidHCID 199401P,P-Diphenylphosphinic azideHCID 194216391-[3,3-Bis(3-chlorophenyl)acryloyl]piperazine

Product 1

HCID 194216551-[3,3-Bis(3-chlorophenyl)acryloyl]-4-(3,4-dimethoxybenzoyl)piperazineYield 94.6%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

0.44 ml of diphenylphosphoryl azide and 0.545 g of 1-[3,3-bis(3-chlorophenyl)acryloyl]piperazine (prepared as described in Preparation 111) were added to 10 ml of a methylene chloride solution containing 0.25 g of 3,4-dimethoxybenzoic acid and 0.38 ml of triethylamine, and the reaction mixture was stirred for 16 hours at room temperature. At the end of this time, the mixture was washed with 10% w/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium bicarbonate and with water, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by medium pressure chromatography using two Lobar B columns eluted with mixtures of hexane and ethyl acetate ranging from 1:2 to 1:4 by volume, to give 0.682 g of the title compound as a white powder.

Workup

  1. washAt the end of this time, the mixture was washed with 10% w/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium bicarbonate and with water, in that order
  2. dry with materialafter which it was dried over anhydrous sodium sulfate
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customthe resulting residue was purified by medium pressure chromatography
  5. washeluted with mixtures of hexane and ethyl acetate ranging from 1:2 to 1:4 by volume

Sources & evidence

ORD record
ord-df5cbb9bcfa74d6aa8890312730b16f2
Source dataset
uspto-grants-1994_11
Patent number
US05369106

Reaction notes

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